Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

被引：39
作者：
Berkenbusch, T [1 ]
Bruckner, R [1 ]
机构：
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
来源：
TETRAHEDRON | 1998年 / 54卷 / 38期
关键词：
asymmetric synthesis; hydroxylation; lactones; osmylation; silicon and compounds;
D O I：
10.1016/S0040-4020(98)00687-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for synthesizing optically active trans,trans-configurated alpha,beta,gamma-substituted gamma-lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix alpha (AD mix beta) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li-2(Me2PhSi)(2)Cu(CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9-11. They furnished the title compounds after oxidative removal of the Me2PhSi group. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：11461 / 11470
页数：10
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